You get the feeling like this guy was the Mitt Romney of the Civil War era, because he did some good things but then kept managing to screw himself over. Born in Massachusetts, he served in the state House of Representatives for one year before joining ranks with the anti-slavery movement. But he wasn’t some foot soldier; after the Kansas-Nebraska Bill was passed he up and moved to Kansas as part of the abolition crusade and employee of the New England Emigrant Aid Company. He also served as a town mayor and helped out with famine relief in 1861.

If only he’d stopped there. Because throughout the ’50s and through the Civil War as well, Pomeroy got involved in a lot of shady investment deals with railroads, coal mines, bridges, etc., so much so that the 1860 federal census in Kansas called him “The Speculator.” The problem with all this is when he tried to run for Senate, he’d already made a lot of enemies. Money quote from one of those enemies, John Ingalls: “If abdomen was a test he [Pomeroy] would be sure to triumph, but as brains enter into the contest some what, his chances are small.”

Still, he was selected in 1861 and served until 1873 when he was accused of buying votes in the legislature and replaced as senator by none other than John Ingalls. Ouch.

The man lives on, though, as the fictionalized inspiration for a corrupt politician in Mark Twain’s The Guilded Age. Can’t get much better than Mark Twain, right?